


Date or Dare

by destieldrabblesdaily



Category: Supernatural
Genre: Alternate Universe - High School, M/M
Language: English
Status: Completed
Published: 2014-09-27
Updated: 2014-09-27
Packaged: 2018-02-19 00:49:35
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,917
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2368109
Author URL: https://archiveofourown.org/users/destieldrabblesdaily/pseuds/destieldrabblesdaily
Summary: <blockquote class="userstuff">
              <p>After a dare with his friends, the popular Dean Winchester takes nerdy Castiel Novak out on a date to earn himself some quick money. However, things get rather complicated when Dean starts falling for the guy who was only supposed to be part of a bet...</p>
            </blockquote>





	Date or Dare

Dean nervously fumbled with the menu in his hands. It should be easy enough; pick something to eat and get on with it. The issue was that Dean was  _distracted._  Distracted by the pretty blue eyes that belonged to his  _date_. Those eyes were big and clear behind a pair of outdated glasses as Castiel studied his own menu.

They were at a nice little Italian restaurant; a perfect place for a first date. But the truth was that this was not a _date_. It was a  _dare_.

From the corner of his eye, Dean could see the table not too far from theirs where Meg and Ruby were sitting, giving Dean the thumbs up and making funny faces at him whenever Castiel wasn’t looking.

This was so  _awkward._  It had started out all fun and games; a game of truth or dare with a couple of friends at a party, where Ruby had dared Dean to take the biggest nerd of the school out on a date. Needless to say, Dean had told her ‘no way’. But then some of his other friends had started to interfere, and all of them had been willing to pay good money to see it happen. Benny, Victor, Meg, Tessa… And yeah, with the promise of  _a hundred bucks_ , Dean hadn’t been able to resist, and he’d  _agreed_. Who cared if one nerdy guy’s feelings got hurt?

So here they were; Dean on a date with Castiel, while Ruby and Meg were there as witnesses to see if he was actually going through with it.

“What are you having, Dean? I’m having trouble deciding what I want, it all sounds very good.”

Dean’s eyes flew up at the deep sound of Castiel’s voice. Castiel smiled at him. It was that genuine, timid smile that Dean had already labeled as  _typical-Castiel_. It made Dean’s mouth turn dry, and he wasn’t even sure why.

“I- I’m not sure yet, Cas… Still deciding.” Dean muttered, abruptly averting his gaze.

It had only been thirty minutes since Dean had picked Castiel up, and already, Dean had some strange fascination with the dark-haired boy. This was going to be way harder than Dean had initially thought, mostly due to a few unexpected  _complications._

A quick survey of things that Dean had not counted on when he’d asked Cas out with the simple goal of collecting that money: Castiel’s  _eyes_ , and how stunning they were from up close, even from behind those glasses. Seeing Castiel now that the boy had actually made an effort to dress up for once, wearing a well-fitting blue button up shirt and jeans, instead of a dorky sweater. Castiel’s  _voice_ , warm, and friendly, and inviting. And on top of that; the fact that Cas was overall incredibly  _nice_.

Dean had never before made an effort to talk to Castiel, and so all of this came out of the blue.

“I think I’ll go for pizza, you can never go wrong with pizza.” Castiel mused, again dragging Dean out of his thoughts.

In the background, Dean recognized Ruby’s giggle. He purposely didn’t look at the girls though, because this was already nerve-wrecking enough as it was.

“Ehm yeah… Pizza is good.” Dean replied lamely, putting down his menu. “Can never eat enough pizza.”

Castiel laughed softly. “I wouldn’t be too sure about that. A few weeks ago my brother Gabriel ordered pizza for us via the internet, he accidentally typed  _twenty_  instead of  _two_ … Mom was  _furious_.”

Dean couldn’t help but laugh as he imagined a pizza delivery guy standing at Cas’ door with no less than twenty pizzas. Castiel laughed along, and  _god_ , that was an alluring sound.

A waitress interrupted them to take their orders, but when she left again, the conversation was easily picked up.

“Yeah, brothers… Can’t count on them to get anything right, can you.” Dean said, jokingly. “My little brother Sammy can be such a pain in the ass. I love the kid to pieces though, even when he keeps me up all night to ask me where the universe ends, or how cheese is made…”

That got another laugh out of Castiel, and it gave Dean a bigger thrill than he would like to admit.

“Your brother is asking the real questions.” Cas said, grinning. “Although I am curious now, where does the universe end, Dean?” He added playfully.

Dean chuckled. “Hell if I know, I still need to figure that one out myself.”

After that, they babbled about  _everything_  and  _nothing_. From brothers they went to family, from family they went to personal interests, and from there they went to movies and music they liked. To Dean’s immense surprise, they even had some favorite movies in common.

The pizza arrived, but even then they were more busy with talking than eating.  In fact, Dean was so engrossed in his conversation with Cas, that he had entirely forgotten why he was here to begin with. All of the sudden, he was cruelly reminded of his mission when he heard Meg’s high-pitched giggle in the distance.

_A dare_ … It was a dare.

Dean fell silent in the middle of a sentence when the truth crashed down on him, but Castiel’s eyes stayed locked with Dean’s. Blue held green, mixing so perfectly that it made Dean’s spine tingle.

“Are you alright?” Cas asked tentatively, sounding worried. “You look like you’ve seen a ghost.”

Dean dismissively shook his head. “No, Cas. I’m good… I just… I’m having a good time.” He blurted out.

Castiel beamed at him. “Me too, Dean. Thank you, for asking me out… No one ever does.”

And Dean’s heart was sinking all the way to his stomach. Castiel was so open and honest, and  _positive_. If Dean had felt guilty before, he felt like an absolute  _monster_  by now. Castiel deserved so much better. He deserved to go on dates  _all the time_. He was funny, and clever, and what the hell did it even matter if he wore dorky clothes at times, or that he had those nerdy glasses? Dean couldn’t remember having such a good time with anyone on a date  _ever_ , and wasn’t that the only thing that mattered?

On an impulse, Dean’s hand gravitated to Castiel’s hand where it was casually resting on the table. His fingers enveloped Castiel’s, and it was easy as breathing; easy as if this was where they belonged. Castiel smiled impossibly wider, peeking up at Dean from under his lashes.

Dean hadn’t noticed how far they’d both been leaning in over the table, until he could literally  _feel_  Cas’ breath against his lips. Inevitably, their lips met in the middle. Dean wasn’t sure how it happened, or who went in first. And it didn’t matter, because all Dean cared about was that Castiel’s glorious lips were at last moving against his… He closed his eyes, so that he could focus on nothing but the pleasure. Cas hummed into the kiss, sending vibrations through Dean’s entire body…

“Holy Christ, Winchester! Stop before you  _hurt_ yourself!” Ruby’s voice ended the moment, and Castiel pulled back as if he’d been burned.

“Ruby… Please don’t…” Dean begged as he looked up at Ruby and Meg who were staring down at him and Cas.

Ruby rolled her eyes. “I mean it, dude. Holding hands with the geek would’ve been enough to get you those hundred bucks. But hey, you earned them  _fair and square_.” She said, offhandedly throwing a couple of bills onto the table.

“Enjoy the rest of your night, boys.” Meg said in a sing song voice as she looped her arm through Ruby’s and pulled her friend towards the exit.

Both girls were giggling as they left the building, but Dean felt like his insides had turned to  _stone_. Castiel was staring at him, the look in his cerulean eyes hurt and empty.

“Oh…” Cas whispered bleakly as he bit his lip. “Of course… That was… that was very  _stupid_  of me. To believe that you actually… God, I am so  _stupid_.”

With that, Cas rushed up from the chair and half-ran out of the restaurant before Dean had a chance to say anything. Once Dean’s brain caught up, he jumped up from his seat as well, running after Castiel, not even bothering to take the money. Because  _no_ , Castiel was not the stupid one here _. Dean_  was the stupid one, for being a heartless douchebag to a boy who didn’t deserve to be the victim of one of the pranks of the popular clique.

Dean slammed the door of the restaurant closed behind him. It was raining outside, and Dean shivered as the cold drops of water hit his face. He spotted Castiel not too far away, sitting on the porch steps of a bookstore on the other end of the street. The store was closed, the windows dark. Dean jogged up to the other boy, who was looking like a drowned cat, the rain relentlessly pouring down on him as he sat there, head buried in his hands.

“Cas…” Dean whispered the name cautiously as he squatted in front of Castiel, placing both his hands on Cas’ knees to keep himself balanced.

Castiel reluctantly glanced up, his cheeks wet, tears mingling with rain.

“Please leave me alone, Dean…” Castiel pleaded, his entire frame shivering. “I get it… I was a bet. Ask out the freak and make some money! It’s fine, I should’ve known better after all these years…”

“No!” Dean called, voice raspy. “No Cas, I… That’s how it  _started_ , but I never would’ve kissed you if I didn’t… If I didn’t actually  _like_  you… I just… You caught me by surprise… I thought I could buy you some dinner, win my bet and forget about it! But then you… You turned out to be  _amazing_ …”

Cas eyed Dean skeptically as he weighed Dean’s words. Wet strands of dark hair were clinging to his forehead. Dean reached up to gently stroke them out of Castiel’s eyes, then readjusted Cas’ glasses before they could slide down the boy’s nose.

“I’m  _so_  sorry, Cas…” Dean murmured, never taking his eyes off of Castiel’s face. “I have never regretted anything more in my life, I  _swear_.”

Castiel sighed, a weary look on his face. “How do I know you’re telling  _the truth_  this time?”

That was a good question… Dean turned that crucial question around in his mind, multiple times. They were both soaked by now, their clothes and faces dripping.

“You  _can’t_  know, Cas…” He admitted after a long moment. “But I  _promise_ , if you give me  _one chance_ , just one… I promise I won’t screw it up! I want to take you on another date, a  _real_  one. And I want to watch movies with you, and talk to you, and hold your hand, and  _kiss_  you, and… Hmmp…”

Dean gulped when he was cut off by Castiel’s lips as they crashed into his own with serious force. The kiss was messy, their lips and faces slippery from the rain, noses bumping clumsily. And yet it was the best kiss Dean had ever received.

When a need for oxygen made them part, Cas rested his forehead against Dean’s.

“I’m sorry, Cas…” Dean said for the second time that night, breathing the words against Castiel’s lips.

Castiel smirked, his tears forgotten. “Oh, I know… You have the rest of your life to make up for it…  _Starting now_.”

And Dean? Dean intended to do  _just that…_

**Author's Note:**

> For more Destiel stories, follow destieldrabblesdaily.tumblr.com


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